Hydrogen-Bonding-Mediated Solid-State Self-Assembled Isoepindolidiones (isoEpi) Crystal for Organic Field-Effect Transistor

Haichang Zhang; Kewei Liu; Kuan Yi Wu; Yu Ming Chen; Ruonan Deng; Xiang Li; Hailiang Jin; Si Li; Steven S.C. Chuang; Chien-Lung Wang; Yu Zhu

doi:10.1021/acs.jpcc.7b11992

Hydrogen-Bonding-Mediated Solid-State Self-Assembled Isoepindolidiones (isoEpi) Crystal for Organic Field-Effect Transistor

Haichang Zhang, Kewei Liu, Kuan Yi Wu, Yu Ming Chen, Ruonan Deng, Xiang Li, Hailiang Jin, Si Li, Steven S.C. Chuang, Chien-Lung Wang, Yu Zhu^*

^*Corresponding author for this work

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

28 Scopus citations

Abstract

Novel pigments isoepindolidiones (isoEpi) and di-tert-butyl quinolino[8,7-h]quinoline-1,7-diyl bis(carbonate) (isoEpi-Boc) were synthesized and characterized. The spectroscopic characterizations indicated that the tert-butyloxycarbonyl (t-Boc) units could be removed from soluble isoEpi-Boc by thermal annealing, forming insoluble isoEpi with hydrogen bonding. A solid-state isoEpi-Boc crystal to isoEpi crystal transition was observed during the annealing process and the molecular packing was significantly changed. With the emergence of hydrogen bonds, the isoEpi molecules were arranged into a brick-in-wall structure with π-stacking along the crystal growth axis, leading to a significant enhancement of charge mobility along the crystal growth direction (the hole mobility from 3.4 × 10^-4 to 0.32 cm²/(V·s), and the electron mobility from nondetectable to 5.6 × 10^-3 cm²/(V·s)). The results indicate that isoEpi is a promising chromophore for organic field-effect transistor (OFET). The crystal-to-crystal transition driven by the formation of hydrogen bonds is a unique method for modulating the charge transport properties in organic semiconductive materials for OFET devices.

Original language	English
Pages (from-to)	5888-5895
Number of pages	8
Journal	Journal of Physical Chemistry C
Volume	122
Issue number	11
DOIs	https://doi.org/10.1021/acs.jpcc.7b11992
State	Published - 22 Mar 2018

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title = "Hydrogen-Bonding-Mediated Solid-State Self-Assembled Isoepindolidiones (isoEpi) Crystal for Organic Field-Effect Transistor",

abstract = "Novel pigments isoepindolidiones (isoEpi) and di-tert-butyl quinolino[8,7-h]quinoline-1,7-diyl bis(carbonate) (isoEpi-Boc) were synthesized and characterized. The spectroscopic characterizations indicated that the tert-butyloxycarbonyl (t-Boc) units could be removed from soluble isoEpi-Boc by thermal annealing, forming insoluble isoEpi with hydrogen bonding. A solid-state isoEpi-Boc crystal to isoEpi crystal transition was observed during the annealing process and the molecular packing was significantly changed. With the emergence of hydrogen bonds, the isoEpi molecules were arranged into a brick-in-wall structure with π-stacking along the crystal growth axis, leading to a significant enhancement of charge mobility along the crystal growth direction (the hole mobility from 3.4 × 10-4 to 0.32 cm2/(V·s), and the electron mobility from nondetectable to 5.6 × 10-3 cm2/(V·s)). The results indicate that isoEpi is a promising chromophore for organic field-effect transistor (OFET). The crystal-to-crystal transition driven by the formation of hydrogen bonds is a unique method for modulating the charge transport properties in organic semiconductive materials for OFET devices.",

author = "Haichang Zhang and Kewei Liu and Wu, {Kuan Yi} and Chen, {Yu Ming} and Ruonan Deng and Xiang Li and Hailiang Jin and Si Li and Chuang, {Steven S.C.} and Chien-Lung Wang and Yu Zhu",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = mar,

day = "22",

doi = "10.1021/acs.jpcc.7b11992",

language = "English",

volume = "122",

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journal = "Journal of Physical Chemistry C",

issn = "1932-7447",

publisher = "American Chemical Society",

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T1 - Hydrogen-Bonding-Mediated Solid-State Self-Assembled Isoepindolidiones (isoEpi) Crystal for Organic Field-Effect Transistor

AU - Zhang, Haichang

AU - Liu, Kewei

AU - Wu, Kuan Yi

AU - Chen, Yu Ming

AU - Deng, Ruonan

AU - Li, Xiang

AU - Jin, Hailiang

AU - Li, Si

AU - Chuang, Steven S.C.

AU - Wang, Chien-Lung

AU - Zhu, Yu

PY - 2018/3/22

Y1 - 2018/3/22

N2 - Novel pigments isoepindolidiones (isoEpi) and di-tert-butyl quinolino[8,7-h]quinoline-1,7-diyl bis(carbonate) (isoEpi-Boc) were synthesized and characterized. The spectroscopic characterizations indicated that the tert-butyloxycarbonyl (t-Boc) units could be removed from soluble isoEpi-Boc by thermal annealing, forming insoluble isoEpi with hydrogen bonding. A solid-state isoEpi-Boc crystal to isoEpi crystal transition was observed during the annealing process and the molecular packing was significantly changed. With the emergence of hydrogen bonds, the isoEpi molecules were arranged into a brick-in-wall structure with π-stacking along the crystal growth axis, leading to a significant enhancement of charge mobility along the crystal growth direction (the hole mobility from 3.4 × 10-4 to 0.32 cm2/(V·s), and the electron mobility from nondetectable to 5.6 × 10-3 cm2/(V·s)). The results indicate that isoEpi is a promising chromophore for organic field-effect transistor (OFET). The crystal-to-crystal transition driven by the formation of hydrogen bonds is a unique method for modulating the charge transport properties in organic semiconductive materials for OFET devices.

AB - Novel pigments isoepindolidiones (isoEpi) and di-tert-butyl quinolino[8,7-h]quinoline-1,7-diyl bis(carbonate) (isoEpi-Boc) were synthesized and characterized. The spectroscopic characterizations indicated that the tert-butyloxycarbonyl (t-Boc) units could be removed from soluble isoEpi-Boc by thermal annealing, forming insoluble isoEpi with hydrogen bonding. A solid-state isoEpi-Boc crystal to isoEpi crystal transition was observed during the annealing process and the molecular packing was significantly changed. With the emergence of hydrogen bonds, the isoEpi molecules were arranged into a brick-in-wall structure with π-stacking along the crystal growth axis, leading to a significant enhancement of charge mobility along the crystal growth direction (the hole mobility from 3.4 × 10-4 to 0.32 cm2/(V·s), and the electron mobility from nondetectable to 5.6 × 10-3 cm2/(V·s)). The results indicate that isoEpi is a promising chromophore for organic field-effect transistor (OFET). The crystal-to-crystal transition driven by the formation of hydrogen bonds is a unique method for modulating the charge transport properties in organic semiconductive materials for OFET devices.

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ER -

Hydrogen-Bonding-Mediated Solid-State Self-Assembled Isoepindolidiones (isoEpi) Crystal for Organic Field-Effect Transistor

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